Dungeons, Dragons, And Devious Archangels
by KittyKat757
Summary: Sam, Dean, Charlie, Bobby and Castiel all sit down in the bunker to play Dungeons and Dragons, but what happens when a certain Archangel turns up and transports them into their game?
1. chapter 1

**A/N: This idea popped into my head when I was reading a Sabriel fic and I just _loved_ the idea of it... Admittedly it's inspired by the Futurama movie "Bender's Game" because that movie is awesome. I don't know... This is going to be a multi-chapter thing but I have to plan it out a little so I can get a feel of what the "quest" will be. Just FYI I've never actually DM'd before so if you notice anything weird then that's why. I hope you like this because it's gonna be _fuuuuuun_ to write! Oh! And umm... This is a bit of an AU since some of my favourite characters never died (*shakes fist at writers*) so enjoy!**

XXX

"Wait a minute, what am I doing again?" Dean asked as he studied the strange dice in his hand.

Charlie rolled her eyes, "you're rolling a perception check, dumbass. Just roll the damn thing," she replied, waving her hand in a 'hurry the hell up' gesture.

Dean did as he was told and rolled the dice, "uhh... One... Is that good?" Charlie shook her head and smiled.

"You see absolutely nothing." She stated simply, "Sam, your turn," she added, turning towards the younger Winchester.

Sam nodded, "I look around the forest and-"

"Sam, we are not in a forest... We are in the bunker," Cas interrupted, tilting his head in Sam's direction.

"Cas, for the last time, it's just pretend. Sam, continue" Charlie explained, gesturing towards Sam to resume his turn.

"I look around the forest and see if I can find a path," the Winchester replied, Charlie motioned for him to roll his d-twenty. "Sixteen" he added, glancing down at the die before looking back up into Charlie's face, awaiting her answer.

"You look around, it's a pretty typical forest, you can see the faint traces of a path stretching to your left."

Sam nodded, seemingly satisfied with the red-head's description.

"Bobby? You ready?" Charlie asked the older hunter, smiling when the bearded man rolled his eyes.

"This game don't make a lick 'a sense... Spells and crazy dice and whatnot, what idjit designed this thing anyway?" Bobby grumbled, holding up the d-twenty and eyeing it as if it had personally offended his favourite hat.

"The 'idjit' that you speak of, is Gary Gygax, one of the most brilliant people ever to grace this Earth with his presence," Charlie replied, "now what do you do, Bobby?" She added.

"I uhh... I start to follow the path to see if I can find a way out of the forest," Bobby finally decided after about thirty seconds of silence.

"Roll," Charlie replied simply, looking down at the d-twenty as it rolled across the table.

"Two," Bobby informed her.

"You attempt to follow the path but fall flat on your face and knock yourself out for a few minutes." Bobby grumbled under his breath and glared down at the dice again. "Cas, your turn."

"I still fail to see the point of this game..." The angel admitted, picking up the dice and examining it's peculiar shape.

"It's just for fun, Cas. Blow off some steam, have a few laughs, that sort of thing." Charlie clarified, flashing Castiel a wide smile.

Cas nodded, "I would like to... Attempt to follow the path, preferably without rendering myself unconscious in the process." Cas finally decided, taking the hint from the previous plays and rolling his d-twenty. "Eighteen," he added after the object had come to a stop.

Charlie nodded, "you successfully follow the path -without knocking yourself out- and see that there is an entrance to a dungeon a bit ahead. Everyone, discuss what to do."

"I say we go in there, plow our way through whatever fuglies we find, and get the loot!" Dean exclaimed with a grin, seemingly becoming excited at the prospect of a dungeon crawl.

"Sounds like a plan, it'd probably be a good idea to level up my character," Sam said.

"I concur. Bobby?" Cas interjected. The older hunter grunted in affirmation and they all turned towards Charlie again.

"Roll," she stated, bringing out a sheet of paper and a pencil.

"Nineteen," Sam said happily.

"Seventeen," Dean chimed in happily.

"Fourteen," Cas added.

"...Three..." Bobby sighed, earning a laugh from the rest of the group.

"Sam, Dean and Cas successfully enter the dungeon, Bobby falls on his face again." Charlie described once her laughter had mostly subsided, just causing another round of giggles to erupt from around the table. Bobby grumbled again and sank lower into his chair, arms crossed.

"I go back and pick Bobby up and put him on my shoulders, then re-enter the dungeon and catch up with Cas and Sammy." Dean said once they had all stopped laughing and it was his turn again, he rolled the dice and smiled when it showed an eighteen.

"You all enter the dungeon and move down a mostly dark hallway, though you can see torchlight ahead."

"Let's go already!" Dean exclaimed.

Sam smiled at his brother and looked towards Charlie again, "I go ahead and see what I can find," He said. The red-head gestured towards his d-twenty and he rolled. "Twenty," he added, happy he had gotten the highest number possible.

"You silently creep through the hallway and peek into the room ahead, there are three skeletons, each one armed with a short sword," Charlie supplied. "Cas, your turn," she added, glancing toward the angel.

"I follow Sam and attack one of the skeletons." The angel said in that flat tone of his, though the glint in his eyes told off the fact that he was a little excited.

"Roll to see if you hit it."

"Nineteen,"

"Roll for damage."

Castiel rolled the d-ten in front of him, "nine."

"Add your attack bonus."

"Eleven."

"You smash the skeleton's head into pieces with your Warhammer, but he still isn't dead. Bobby, your turn."

"Good hit, Cas!" Dean praised, smiling at the angel and earning a small smile in return.

"I hit the same sonovabitch Cas just dealt with."

"Roll."

"Oh for the love of... Six..."

"You hit your foot instead... Sorry Bobby..."

"Wait so is it my turn again now?" Dean asked, growing a little impatient.

"Nope, since Bobby missed, it's the skeleton's turn." Charlie corrected, picking up her own d-twenty and rolling it, "crap. Nat-one... The skeleton misses and ends up slamming into the wall and taking three damage, it's dead." She added, "okay, Dean, your turn."

"I attack the next skeleton in line." Dean decided quickly.

"You know what to do..."

Dean rolled the dice in the appropriate order.

"You grab your bow and plant an arrow right in the centre of the skull, cracking the bone and making the skeleton crumble to a pile of dust on the floor, critical hit!"

Sam and Dean high-fived, seemingly pleased with this outcome.

"Okay, Sam, last skeleton." Charlie said happily.

Sam nodded and rolled his dice as Dean had.

"You take your battle-axe and drive it into the skeleton's ribs, he still isn't dead but several ribs have broken and he is now missing an arm from the force of the blow."

"Cas, you wanna finish this for me?" Sam encouraged, smiling at Castiel as the angel began rolling his d-twenty.

"Yes, Sam, I shall 'finish it off' so to speak-"

" _Helloooooooo!_ " A voice suddenly sing-songed from behind them and they all jumped, turning towards the intruder, Sam and Dean grabbing guns that were hidden under the table while Cas produced his angel blade.

"Gabriel?!" Everyone exclaimed in unison upon seeing who it was.

"The one and only," the archangel said with a wink. "Ooh, DnD huh? Looks like fun!" He added, an evil smirk suddenly spread across his face and before anyone could do anything, he snapped his fingers and the world went black.

XXX

 **A/N: did ya' catch my Futurama reference in there?! Also I noticed that Bobby's turn came before Cas's the first time but I'm too lazy to change it so everyone will just have to deal with a continuity error or stop reading. *blows raspberry* _anyway_ I hope you guys liked the first chapter!**


	2. chapter 2

**A/N: okay, my friend has informed me that it's actually written as d20, though because I am too lazy to change it, you will all have to live with that spelling error in the first chapter. I'm also gonna need her to help me out with my lingo a little but whatever... Anyway, enjoy!**

XXX

Dean opened his eyes and grunted, God, he felt like he weighed a million pounds... And wait, when did he fall asleep?

"Dean?" He heard Sam call, the elder Winchester turned his head and froze at what he saw. His little brother had long ears -what was he a Vulcan?- and his hair reached his chest now, he was clad in a forest green cloak and a brown tunic.

"Dude, Sammy, why the hell do you look like you just stepped out of a 'Lord Of The Rings' box set?" Dean said, puzzled at his brother's sudden change in appearance.

"Says the guy who looks like one of the mountain trolls..." Sam replied. Well at least his sass wasn't affected- wait... What did he mean by mountain trolls?

"The hell are you talking abou-"

Dean was interrupted by a loud squealing noise next to him, he and Sam quickly wheeled around to see Charlie waving her hands around with a huge grin on her face.

"What the hell?!"

They all turned to see Bobby getting up from the ground next to them and... Oh. Well that was certainly different. Bobby stood there -as pissed as they'd ever seen him- standing at around four foot three with a much fuller beard and a dark blue hood on his head.

"What did you idjits do this time?!" Bobby snapped.

"Apparently Gabriel is alive and now we're lost," Dean grumbled, turning to stare at his brother again because this was all just much too bizarre and he feared that if he kept looking at Bobby he would burst out laughing.

"Well that's just- wait a minute, where's Cas?"

Sam heard movement beside him and glanced down at the still unconscious figure next to him. It looked like Cas but with short red horns, a thin tail, and cloven hooves instead of feet.

"What the fuck?!" Dean exclaimed upon noticing these things as well. "Why is Cas a demon?!" He added, turning towards Charlie in hope of an answer.

"He isn't a demon, he's a Tiefling. They have a bit of demon in them further up the family tree but they usually aren't evil, someone should wake him up but uhh... Brace yourself for when he opens his eyes, okay?"

"Wait, why-"

Dean got his answer when Cas's eyes slowly opened and he froze at what he saw. His eyes were bright yellow-gold in colour, no whites and no pupils, just gold.

"D-Dean? What's going on?" Cas asked, confused by the horrified and shocked faces that were surrounding him.

It took a minute or two before the hunter could even form words, still in a bit of a shocked daze he answered shakily; "Gabriel... He uh... I think he trapped us in our game..."

Cas nodded, then paused, "why are you all looking at me like that?" He asked since nobody had stopped staring at him yet.

"If we can find a mirror then we can all get a good look at ourselves, seeing as we seem to have undergone some crazy changes..." Sam reasoned logically. "I think I see a village over there," he added, spying the outline of buildings on the horizon. The group nodded and followed as Sam began to lead the way towards the village, all curious and just a little scared at what they would find.

XXX

"So... Charlie? Do you have any idea why Cas is..."

"Like that? I don't know, I guess Gabriel just thought it'd be funny to turn the angel into something resembling a demon..." Charlie answered with a shrug. "Why? Does it really bother you _that_ much?"

"I don't know... It's just... _OffPutting_..." Dean explained with a shudder as Cas turned those bright, golden eyes on him again and raised a questioning eyebrow.

"Are you alright, Dean?" He asked.

"Y-yeah, Cas... Your eyes are just freakin' me out a little..." Dean said dismissively, resisting the urge to flinch when it seemed like Cas hadn't blinked in minutes.

"My eyes? What's wrong with my eyes?"

"They're kind of... Bright yellow, Cas..." Sam interjected.

Cas turned questioning eyes on the younger Winchester and Sam tried to find something reflective, sadly coming up with nothing, he did find a bag of gold and silver though, which he imagined would be useful later.

They all decided to walk faster in order to find a mirror, or else they would probably all be slowly going crazy.

XXX

The group finally made it into the village and _oh_ the looks they got! Hard glares, quizzical, curious, or fearful stares, all in all it made the small party a little uncomfortable.

They all trudged into an armoury and sighed happily when they noticed a large mirror at the back of the shop. They let Dean and Cas go first since their changes were the most drastic and Dean's face was surely one to behold when he witnessed the fact that he seemed to have sprouted thick, pointed teeth out of a slightly underbitten jaw, along with the fact that his skin had changed to a light green-ish colour.

"What the hell?!" He exclaimed, tentatively touching one of the large fangs now protruding from his mouth.

Cas's reaction wasn't much better to be honest... He squeaked and jumped backwards when he saw his own eyes and started shaking when he saw the rest of his physical appearance. Some things were still the same though, lean yet decently muscular body, ruffled and disheveled black hair, slight five-o-clock shadow and the same rough, gravelly voice.

"Oh God, I look like a demon!" Cas bawled, burying his face in his hands.

"No shit, you're a Tiefling, you idiot." Someone browsing through armour next to their little group said.

"Hey! What the hell is your problem?!" Dean snapped back, wrapping a comforting arm around Cas when he shrank back a little at the stranger's insult.

"Dude, chill out, he's just a piece of Tiefling scum. The product of ancestors who made a deal with a fiend for power. There's no need to get worked up over defending him or anything," the guy replied nonchalantly. Not really surprised by the intensity of the half-Orc's glare, it was pretty common for his species to have that hard look in their eyes.

Dean didn't respond this time, just stepped aside as Sam took his place in front of the mirror, though he did step in front of Cas in a protective manner, putting some distance between him and the stranger who seemed to like insulting Tieflings.

Sam's eyes widened a little when he saw himself, it was strange to see that his ears had elongated and his hair had grown out a bit, but at least he hadn't sprouted demon horns and a tail like Cas, or an underbite and fangs like his brother.

"I actually kinda like it," he said with a small smile.

"You got off easy, Sammy." Dean grumbled.

Bobby didn't step in front of the mirror, he got the gist of it, he didn't want to see himself in this weird state anyway. He noticed none of them actually had any weapons and he intended to rectify that.

"Okay ya' idjits, listen up. We got no weapons and from what little I know from Charlie here, there's a butt-load 'a monsters crawlin' around these parts. So everybody search your pockets and see if you can find any money." The older hunter ordered, determined to get his team on track and out of this crazy nightmare ASAP.

"I've got some gold and some silver." Charlie announced after rooting through her pockets. The rest of the team said the same and they all assumed Gabriel had given them the currency in order to help them out at least a little.

They browsed around the armoury until they found a well made Morningstar for Dean, a large, steel-looking battleaxe and a wooden short bow for Sam, a glaive -Dean picked it out, insisting that he would look awesome using it- for Cas, a greatsword -according to her she had always wanted to use one- for Charlie, and lastly, a war pick for Bobby since he was currently stuck in the body of a dwarf and everyone thought it was fitting.

"That'll be one hundred and twenty-five gold pieces." The person behind the counter said, glancing shiftily around at the party of adventurers.

They all produced their small pouches full of gold and silver pieces, passing them over the counter and receiving their weapons. Each nodding their thanks before leaving the shop.

"Ugh, let's hit the bar..." Dean grumbled, hurrying his party along and into the inn.

XXX

"Round of mead all around!" Charlie called, waving over a bar wench and winking at her. The woman winked back and came back a few minutes later with a round of mead in giant flagons.

"This is what I'm talkin' about!" Dean exclaimed happily as he picked up the beverage and took a large swig.

"Dean, slow down. We do not want you getting intoxicated." Cas said, taking a very tentative sip of his mead.

"Lighten up, Cas. If we're stuck in Dungeons and Dragons anyway, might as well have a little fun!" Dean slurred -that mead sure went through his system quick- happily.

XXX

"Night, guys."

"Goodnight, Sam, Dean, Bobby, Charlie."

After everyone retired to their rooms -Sam and Dean took one, Charlie and Cas took another, while Bobby took the last one since it was a single and he didn't want to be disturbed- they settled into a restless sleep.

XXX

"Cas. Cas, wake up. Cas! Oh for the love of- Cas! Dean's missing!"

Cas woke with a start and sat bolt upright, seeing Charlie staring exasperatedly at him.

"What?! Where's Dean?!"

"Relax, Cas. I had to wake you up, sorry for scaring you."

"It is fine, Charlie..."

"You're a real heavy sleeper, Y'know that, Cas?"

"I am aware, yes..."

"And you snore."

"Is that really important?"

"No, come on, let's go wake up Sam and Dean, you _know_ they're still asleep..."

XXX

 **A/N: do you _know_ how much research I've randomly started doing for this story?! I have so many tabs open on Google Chrome it isn't even funny... But yeah, hope you guys enjoyed the second chapter! Oh and you know me, I couldn't resist putting in a little protective!Dean simply because I can.**


	3. chapter 3

**A/N: hi everybody! (Insert "Hi, Doctor Nick!" Here) I was over at a friend's house playing DnD the other day, (we killed a manticore and one of my teammates shoved a sword up its butt because we are incredibly immature) and I got inspired to write for this again! So yeah, have fun!**

XXX

"Ugh, God. Charlie it's like five in the morning, why'd ya' have to wake us up?..." Dean groaned, trying to swat away the red-head's hand that was currently trying to shake him awake while Cas attempted to wake up Sam -who had a much better reaction considering that he was a morning person-. Dean practically heard Charlie's eye-roll as she explained again.

"I told you. Bobby wants us up and moving relatively soon so we can figure out why Gabriel put us here." The half-Orc grunted again and finally sat up. "He lives!" She said sarcastically, moving off of the bed.

Dean rolled his eyes at her and glanced over at Cas, still slightly unsettled by his demon-like appearance but slowly starting to get used to it. In all honesty it was actually pretty cool. Dean was drawn out of his musings by Charlie loudly clearing her throat and motioning for him to get a move on once she had his attention.

Sam stretched and got out of bed without complaining, grabbing his supplies and making his way to Bobby's room to get him before heading down to the tavern with the rest of his group for breakfast.

XXX

The tavern was less busy than it'd been last night, but still quite bustling. People and creatures of all shapes and sizes sat sharing pints of mead, -wait a minute, wasn't it only five in the morning?- eating, and talking about things that would only be common in a fantasy world.

The small party made their way over to one of the large, well-worn, scrubbed oak tables that littered the tavern and sat down, each ordering their preferred breakfast before beginning to discuss their plan of action.

"So.-" Charlie started, making sure she had everyone's attention before continuing. "-What exactly are we going to do? I'm pretty sure Gabriel wants us to complete a quest in order to get out of here, and that means fighting some giant monster, so we should probably get our hands on some sort of newspaper in order to try and find what will lead us to said monster."

The rest of the group nodded their approval, seemingly satisfied with her plan.

"Well you know more than any of us about this game, Charlie. So you should lead the way on this quest of ours," Cas said thoughtfully, attempting to ignore the stares he was getting from some of the bar patrons. What was it with this town and Tieflings?!

The group nodded again before a loud shout interrupted their conversation.

"Hey! Tiefling!"

Castiel's head turned and he tilted his head in confusion when he recognized the man who'd insulted him back at the armoury.

"Can I help you?" Castiel asked.

"What're you doing here, Tiefling? Shouldn't you be off theivin' or assassinating somebody?" Came the slurred and bellowed reply. Seriously, what was this guy's deal?

"Hey, back off!-" Dean exclaimed, hand momentarily going to the handle of the morning star attached to his belt before catching himself and settling for balling it into a fist instead. "-What's your problem anyway?!"

"Mind your own business, half-Orc. This is between me and the demon spawn." The man said, eyes narrowing threateningly at Castiel who tensed and unconsciously reached for his angel blade only to remember he didn't have it.

"You're yelling at and insulting my friend, I'd say it's my business!" Dean retorted heatedly.

"Whatever. If I were you I wouldn't be wastin' my time with _his_ kind though. Bunch of demonic, untrustworthy, no-good wastes of space if you ask me..."

Dean was out of his seat and in front of the guy before he could blink, throwing a punch that landed squarely on the guy's nose.

"Dean, stop!" Cas's voice exclaimed from somewhere behind him. "It's not worth it!"

"Yeah that's right, Teifling, afraid to get your hands dirty arent'cha?" The man leered, smirking even though his nose was beginning to swell from the force of the elder Winchester's punch. While everyone was distracted he quickly threw a punch of his own, hitting Dean in the cheek with a mean right-hook.

"Dean!" Cas shouted urgently, moving to run forward before one of the guy's companions grabbed his tail and yanked him backwards, causing him to yelp in surprise and pain before he was grabbed and thrown into an adjacent table by the surprising strength of his attacker. He groaned and attempted to get up from the remains of the furniture before he was pinned down and a dagger was pressed against his jugular.

The whole bar stopped, all of the patrons frozen in time except for the party of adventurers and their opponents, all but the one with the dagger melting away into thin air. The only sound in the bar being Castiel's laboured breathing as he attempted not to inadvertently cut his throat.

"What the hell?! Get the fuck off of him!" Dean shouted angrily, moving to step forward before the guy holding Cas spoke up.

"Take one more step and I'll slit his throat."

Dean growled but obeyed the order as he stood stock-still, not wanting to put his friend in any more danger than he was already in.

"What do you want." The half-Orc demanded, baring sharp teeth at Cas's assailant and thinking of all the different ways he could tear the guy apart for threatening his family.

"For you dunderheads to get on with the quest already!" The guy replied in a familiar voice. Oh, God, please don't let it be- the figure shifted into the form of the archangel and Dean groaned internally, of course _he_ would be behind this.

"Gabrie-mph!" Cas started before Gabriel slammed a hand over his mouth, winking at him before turning back towards Dean.

"I see you guys have adjusted quickly! I thought it would take more time to get used to Cassie here but it seems I was wrong." Gabriel said, mischief glinting in his eyes as he held down a futilely struggling Castiel, hand still in place to keep the angel from speaking.

"Get off of him, Gabriel." Sam said, apparently suddenly deciding to join the conversation as apposed to just standing there in shock as he had been previously.

"Well don't you look pretty, Sammy? A regular Legolas!" Gabriel replied, turning his whiskey-coloured eyes on the younger Winchester while the older was still glaring at him- if looks could kill...

"Umm, excuse me, Mr. Uhh... Archangel, sir..." Charlie said timidly barely resisting the urge to flinch when Gabriel turned his gaze on her and smirked.

"Charlie Bradbury, right?" He asked, receiving a scared nod from the red-head.

"If you... Wouldn't mind letting go of Castiel then..." Charlie tried to continue, failing to keep her voice calm and eyes widening slightly when the archangel let out a boisterous laugh.

"Fine. I only came to give you guys a message anyway," Gabriel sighed, reluctantly releasing his little brother and smirking when the younger angel gave him a death-glare.

"And what message would that be?" Dean asked gruffly, relaxing slightly now that Cas was out of immediate danger.

"Check your pockets." Gabriel replied simply, and before any of them could ask what that meant, he disappeared. All of the bar patrons unfroze, seemingly having no memory that a fight had taken place and returning to their own little worlds.

XXX

 **A/N: well that's chapter three done! What'd you guys think? Please leave a review and let me know, (and yes I realize I might have put a little bit of unintentional Destiel in there with Dean being the overprotective worried boyfriend that he is but I swear I didn't mean it! I'm trying to keep this story slash-free but it's difficult...) **


	4. chapter 4

**A/N: Okay, chapter four... Tuesday was one of my weekly DnD games (yay!) and I got inspired again. Tuesday's was hilarious and exciting since we were going through a dungeon and I ended up getting a collapsible boat that could talk and sounded like Morgan Freeman and was super sarcastic, one of my friends befriended a mouse that spoke Druish and could use detect magic, and another friend formed an alliance with and now has an army of bats that are immune to magic (God I love this game). (Also another friend stole a bit of my ham but that isn't important) OH and I edited the last line of chapter three so please read that...**

XXX

"What did he mean by check our pockets?" Sam asked curiously, smiling quickly to the bar wench when she brought their breakfast over.

"Well I'm guessing 'check your pockets' does in fact mean check your pockets, Sammy." Dean replied sarcastically before picking up a large piece of bacon and biting into it.

Sam rolled his eyes and picked up his fork, the rest of the group accepting the signal to begin eating.

"We'll look after breakfast," Charlie supplied, dipping a piece of her toast into the yolk of a fried egg and taking a large bite.

"Y'know, Cas, I'm surprised you got anything. I thought you didn't need to eat," the elder Winchester said, smiling slightly when Castiel began to scarf down his food at lightening speed.

"It seems that... Gabriel has... Rendered me more human than I am normally." Cas said through mouthfuls of ham, fried eggs and hashbrowns.

"Well maybe eat a little slower. Don't want you dying on us 'cause you choked on a bunch of ham," Dean teased, though he was only slightly kidding. At the rate Cas was going it wouldn't be soon before some of that food clogged his windpipe. That and he didn't exactly want to clean up the angel's barf if eating like that upset his stomach.

Cas nodded and -albeit begrudgingly- began to eat a more reasonable pace. "I suppose you are right, Dean," He admitted.

XXX

"Okay. Let's see what Gabriel meant." Charlie said, starting to dig through her pockets, quickly followed by the rest of the party.

"The hell?" Dean asked, staring quizzically at the object when he pulled a bright green d20 out of the front pocket of his pants.

"I've got one too," Sam informed, pulling out a similar looking brown dice.

"As do I..." Cas sighed, showing the bright blue d20 in his palm to the rest of the group. Bobby and Charlie were not surprised to find a pair of dice on their person as well -fluorescent pink and indigo-, they all stared at the strangely shaped pieces of plastic. Confused as to why they had them.

"Whatever. M'sure it's nothing" Dean said dismissively, throwing the object behind him before promptly tripping and landing sprawled out, face down on the floor. "Ow." He added unnecessarily.

All eyes turned to the discarded d20, simultaneously widening when they found it had landed on a one.

"Oh my gosh, that's so cool!" Charlie squealed, picking up the die and handing it back to Dean. "I think we have to roll in order to do certain stuff." She clarified after noticing the dumbfounded and confused looks directed at her.

"Oh great..." Bobby grumbled, glaring down at the d20 in his hand with great distrust.

A loud Yelp sounded from their left and the group turned to see Cas had stepped on his tail and his d20 was on the floor, proudly displaying a two.

"I... I was curious..." He muttered embarrassedly, rubbing the sore spot on his tail and scooping up the hunk of plastic again and blushing bright red.

XXX

" _Mysterious Necromancer Continues To Terrorize Forest Under Chrysals Mountain_ " Charlie read aloud from a newspaper they had acquired. "I say we head in that direction."

XXX

"Ugh, finally. I can't wait to get out of this stupid town." Dean said after they had stocked up on supplies and were preparing to leave the small village.

"Oh shut it, Dean, it wasn't _that_ bad." Sam chastised, rolling his eyes at his brother and readjusting the large rucksack on his back.

"Quit yer' talkin' and let's get a move-on!" Bobby said, starting to walk towards the large wooden gates that separated the village from the outside world. Sam and Dean snapped back to attention and hurried to catch up to the rest of their group as they made their way towards the edge of the town.

"Wait up!" Dean exclaimed, quickly hitching up his own backpack and trotting after his family.

XXX

"Ugggghhhh we've been walking for _hours_!" Dean whined, begrudgingly shuffling along behind his party as they made their way through a large forest.

"Dean, this is bad enough without you complaining every ten seconds!" Sam snapped, becoming more and more annoyed with his brother's bad attitude

"I can't help it! I miss my baby! I miss the bunker! I miss _TV_!" Dean bitched, earning either a sigh or a groan from all of the others.

"Does anybody have a spell that'll make him shut up?" Bobby asked hopefully.

"Actually _you_ might at a later level, Bobby," Charlie answered, not missing the glint of fear that momentarily flashed through Dean's bright green eyes. "I'm pretty sure Gabriel made you a wizard." She clarified upon seeing Bobby's slightly confused look. The older hunter nodded curtly and turned back to the path ahead, careful not to let his adopted son see his smirk.

XXX

 _"Are we there yet?"_ Dean asked about forty minutes later, effectively breaking the peaceful silence the group had fallen into.

"We don't even know where _there_ is yet!" Sam exclaimed, giving his brother a stern bitchface.

"Geez, just asking..."

"Dean, I know it is boring but if you would please refrain from complaining that would be greatly appreciated..." Cas suddenly spoke up, turning apologetic yet slightly annoyed eyes on the elder Winchester.

"Sorry, Cas." Dean apologized.

"Oh so you listen to him?!" Sam said disbelievingly.

"He asked nicely, Sammy." Dean replied with a shrug and a smug look at the even stronger bitchface that was sent his way.

"Idjits..." Charlie and Bobby grumbled under their breath in unison.

XXX

Bright afternoon sun shone down from above the canopy of treetops, staving off the last of the morning chill. A lone thrush called and flew into another tree. Of course none of this was noticed by the small party of adventurers as they were busy fighting a small goblin that had jumped out of the underbrush beside their path.

"Just roll the dice, dammit!" Charlie shouted, grabbing her d20 out of her pocket and waiting for the elder Winchester to roll his.

"What if it lands on a low number!"

"Then you'll miss!"

"Fine... Eighteen! Alright you little bastard, let's see whatcha got!" Dean exclaimed triumphantly, grabbing the handle of his Morningstar and charging at the creature with it, the spiked ball upper cutting into its jaw. "Sammy! Your roll!" He added, seeing that the creature was still alive.

Sam quickly dropped the small hunk of plastic onto the forest floor and smiled when it landed on a seventeen. He aimed his short bow and planted an arrow through the middle of the goblin's skull, effectively killing it.

"Good shot, Sammy! Charlie, does he have any loot?"

"Not really... Goblins are pretty common enemies."

"Well that sucks... Anyway let's go, there might be more."

XXX

"I... Believe we should take a small rest here..." Cas said, slumping down in front of a large cave covered by the branches of a weeping willow sitting on top.

"Good idea, Cas." Dean agreed, sitting down as well, quickly followed by Sam, Bobby and Charlie.

XXX

"Hey, Cas? Me, Sam and Bobby are gonna go check out the area okay?" Castiel nodded and watched as the hunters left, turning towards Charlie when she yawned.

"I might need to take a nap..." She admitted sleepily, rubbing at her eyes with one hand.

"Then take one, I will be fine."

Charlie nodded before quickly drifting off to sleep, the sounds of nature acting as the perfect lullaby. Castiel also nodded off after about ten minutes, it was only when he felt something grab his wrist that he blinked his eyes open. What appeared to be a severed hand moving of its own accord was holding down his arm.

"What the?-"

He was cut off by another hand scuttling up on its fingers and latching onto his other wrist, accompanied by a third one that seemed to be waiting for something.

"Char!-" he found out what that something was when the third hand crawled up onto his face and rested over his mouth, effectively stopping him from warning the red-head. Castiel attempted to fight off the strange creatures but to no avail, they seemed much stronger than they looked. The first two hands started slowly but surely dragging him back into the cave, despite his struggling. When he felt a strange heavy feeling wash over him his eyes drifted shut and the world went dark.

XXX

 **A/N: first of all, yes I realize I'm being a little mean to Cas but whatever sue me (I also feel like Gabriel would focus around Cas more since he's his little brother) but anyway. I made _another_ Futurama reference (see if you can spot it). The creatures that were just used are actually called "Crawling Claws" look them up on the DnD wiki for more info since I'm bad at summarizing things. I have another DnD game on Friday so hopefully that will give me some inspiration for the next chapter, bye everybody!**

 **-KittyKat757**


	5. chapter 5

**A/N: hey guys. Got back from DnD a couple of hours ago and wanted to write chapter five. My character and her party met up with a unicorn and a vampire (the unicorn turned into a humanoid) and they are a couple. The unicorn gave my character a super powerful whip and she also now has a moose named Samuel as a mount. So yeah. Anyway I left the last chapter off on a cliffhanger and I hate those myself but I'm a little hypocritical when it comes to writing... But enough of my rambling, enjoy!**

XXX

Castiel cracked one eye open and shut it again, seeing as his vision was too blurry to see. He tried again with both eyes and blinked a few times, eventually getting his hazy vision to clear.

' _Where am I?_ ' He thought, noticing his unfamiliar surroundings. A torch flickered to life by itself and a man in long, dark purple robes stepped out of the shadows.

"Greetings, Teifling," he said "both to you and your human friend." He added, nodding his head in the direction of a still unconscious Charlie.

"Where are we? What've you done to us?" Castiel questioned, balling his hands into fists and unintentionally cracking his tail like a whip on the floor.

"All in good time, my Tiefling friend. First I must ask you a question, what are you doing in my forest?" The man replied, annoyingly calm, in Castiel's opinion.

"My party and I were just passing through, the human and I were simply resting when your creatures grabbed me." Castiel lied, deeming it as a bad idea to tell this man they had come to kill the Necromancer, as he had a sneaking suspicion said Necromancer was standing in front of him.

The man nodded, though he did not look convinced. "If you were simply passing through, why were you carrying weapons?" He asked, gesturing to where Castiel's and Charlie's weapons had been piled haphazardly on the floor.

"There are goblins and other such creatures in this forest. We did not wish to be killed by a lowly bugbear or something similar." Castiel replied, hoping that what he had learned from the Winchesters about distorting the truth was being put to good use. "Now. I have answered your questions. Please grant me and my friend safe passage out of here... Wherever here may be."

"Very well... Y-"

"Cas! Charlie! Where are you guys?!" A voice called from somewhere less deep in the cave. Castiel's eyes widened and he didn't have time to react when he was suddenly thrown back into the rocky wall, remaining pinned there by some unseen force.

' _Just my luck..._ ' Castiel thought angrily, trying to fight off the magic that was holding him in place.

"Liar! Fiend! You were planning on doing away with me, weren't you!" The Necromancer spat, glaring at the Tiefling.

"Cas! _Caaaas!_ Charli- Cas!" Castiel glanced up at the sound of his name being called and sighed in relief when he saw Dean round the corner into the room. "What the hell?!" The half-Orc exclaimed when he layed eyes on the scene in front of him.

"Dean, it's the Necroma-aaaaancerrrrrrr..." Castiel exclaimed before his speech turned to a slur when the same heavy feeling that had caused him to lose consciousness earlier washed over him again and his eyelids started to droop.

"Hey! Stop that, you asshole!" He heard Dean shout. "Cas you better stay awake, you hear me!" Castiel weakly nodded and tried to shake off the drowsiness that was quickly setting in.

A series of grunts and pained shouts brought the Tiefling back to awareness and he struggled to open his eyes. Seeing Dean and the Necromancer doing battle he attempted to help, only to remember he was pinned to the wall. Sighing, he closed his eyes again. It was only when a particularly agonized cry sounded from in front of him and he roughly dropped to the floor did Castiel bother to try and open his eyes again.

"Hey, Cas. That's it. Open those baby-blues for me, huh?" Dean said, ruffling the Tiefling's hair, smiling when all it did was make him groan.

"Dean, m'tired..." Castiel mumbled, all eloquence gone from his speech in his dazed and exhausted state.

"I know, Cas. Let's get you and Charlie outta here, okay?" Castiel nodded, accepting the elder Winchester's help when he assisted in standing up, only to immediately sway on the spot and need to be caught by the arm to keep from falling over. "Woah! Easy there, Cas..."

"I apologize, D'n..." Castiel slurred.

"It's fine, Cas. Just follow my lead, okay?" Dean said, draping one of Cas's arms over his shoulders and placing a hand on the other's waist to steady him. "Heads up, Cas, I'm about to yell, 'kay?" Castiel nodded "SAMMY! GET YOUR ASS IN HERE I NEED SOME HELP!" Dean bellowed.

Sam trotted into the cave and made his way over to his brother. "What do you need help with? Are Cas and Charlie okay?" He asked.

"I've got Cas but can you go grab Charlie? Bastard Necromancer hit 'em with some kinda sleeping spell." Dean replied, adjusting Cas a little since he's started to slip a bit. Sam nodded and walked over to Charlie, picking her up and moving back over to his brother. Dean nodded, signalling for Sam to start going.

"Dean, I... I don't think I can stay awake..." Castiel said, head lolling to the side and resting on the half-Orc's shoulder.

"Okay, Cas," Dean said "you're just lucky I'm a lot stronger here... Go ahead and crash out." With a grateful nod, Castiel let himself go. Hearing Dean chuckle before his eyes closed.

XXX

"Caaas. Cas. Cas, open your eyes. Cas I need you to wake up, okay?"

"Nnnnnnng... No... Go'way..."

Dean chuckled and lightly shook Cas's shoulders again. "C'mon, Cas. Don't make me slap you across the face, remember. Half-Orc strength."

Cas rolled over and groaned, burying his face into the pillow beneath him.

"Okay that's it. Sorry, Cas..."

Dean winced when Cas sat bolt upright after he had slapped him open-palmed across the face. "Oh god. Uh... You okay, Cas? Sorry about that..."

"I'm... I'm fine, Dean... Just a bit startled... Is the Necromancer dead? Where's Charlie?"

"Understandable, yes, and she's over there." Dean said, pointing to where Charlie and Sam were chatting by the doorway. Cas nodded and fell back onto the pillow.

"Okay, up and at 'em, Cas. We should grab some dinner since you've been out for a few hours.

"Okay, Dean."

XXX

 **A/N: yay more accidental Destiel! (I'm so sorry for the non-shippers out there but I _can't help it!_ They're just too in love for their own good!) _ANYYYYYYWAYYYY_ see you guys next chapter!**


	6. chapter 6

**A/N: hey, guys! I know I haven't updated this is a while but here's a new chapter so there ya' go! I keep forgetting to put disclaimers on my stories that I do not own any of the characters (except for random OCs that might show up every once in a while) and I am not making any sort of profit from this fic. All that is mine is the story.**

XXX

"See, I told you you were holding the map upside down!" Sam snapped, snatching the piece of parchment from his brother's hands and rotating it one-hundred and eighty degrees before shoving it into the half-Orc's chest with a large scowl on his face.

"Oh well _sorry_! I'm afraid I'm not used to reading maps since I'm usually _driving_!" Dean yelled, stabbing his finger into his brother's chest.

"Boys, I swear to God if you two don't stop bickerin' I'll-" Bobby was cut off by the sound of laughter, loud cursing and rustling leaves as Dean shoved Sam into the bushes off the left side of the path.

"Are they like this all the time?" Charlie asked Cas under her breath when Bobby had approached the brothers, ranting on about how this was already hard enough without them acting like a couple of children.

"Essentially, yes," he replied with a sigh before moving forward to try and help break up the argument as best he could.

"Okay then..." Charlie thought out loud, shrugging and picking up the map from where it had been dropped on the ground, wiping the dust off before studying it to see which path they should take.

XXX

The fallen autumn leaves crunched with newly laid frost as the small party of adventurers slowly but surely made their way through the rolling, grassy countryside. The worn, well-used dirt road wound through the hills, gaining fresh bootprints, new-

"DEAN I SWEAR TO GOD!"

Oh. Well, I guess that paragraph was getting a little Tolkien-ish anyway... Fine then, let's see what the party is up to since Sam decided to speak up.

"Ugh, what is it now, Sammy?!" Dean said, turning his head to look at his brother who was possibly giving him the best bitchface he'd ever seen.

"If you don't stop making the branches hit me in the face I will drive this god damn battleax into your skull!" Sam groused, making sure to shoot his brother yet another death-glare.

"Dean, Sam, will you _please_ try to refrain from fighting or arguing? I would prefer to spend the rest of our travelling time either in silence or _pleasant_ conversation," Cas spoke up, trying to both politely get his friends to stop fighting and speak sternly to them since they were both grown men and they should know better than to act like this, at least in the company of others anyway.

Dean just blew a raspberry at the Tiefling and crossed his arms in a huff, causing said Tiefling to roll his eyes and turn his attention back to the road ahead.

"Y'know, you guys have a really shitty attitude about our situation..." Charlie piped up, turning around to face the two brothers and beginning to walk backwards.

"Yeah well, we're trapped in a tabletop role-playing game with you as our only source of information, there are monsters _everywhere_ , you and Cas nearly got murdered, I'm stuck in the body of a fucking half-Orc, and Sam's being a bitch. I'd say that's reason enough to have a shitty attitude." Dean counted off his points on his fingers and when he was finished speaking, looked up to find Charlie -as Cas had done- rolling her eyes and turning her gaze back to the road.

"Well, I tried..." He thought he heard her mumble under her breath.

XXX

They stopped under a large fir tree where they'd decided to set up camp for the night, unceremoniously dropping their heavy backpacks and satchels with grateful sighs or pained groans.

"Oh thank fuck!" Dean exclaimed after dumping his backpack with the others'. "I thought I was gonna collapse under the weight of that damn thing! What the hell'd we put in these things, lead?!" He added, glaring at the luggage as though it had just punched him in the face.

"Well, there may be some things made of lead contained within our bags, after all the universe we are currently in seems to be in a medieval-"

"Rhetorical question, Cas."

"Oh. I apologize, Dean..." The Tiefling muttered embarrassedly, tail wrapping around his leg in a rather put-out gesture.

Dean sighed, instantly regretting his harsh tone, "it's fine, Cas. Sorry for snapping at you." He apologized in what was hopefully a softer one.

Cas seemed to relax a little at that, realizing that the half-Orc was probably just tired and cranky from the extremely long walk they had just finished. He nodded and went to help the others with setting up the camp.

XXX

"Charlie, on your left!" Cas notified, falling a couple of steps behind the boar they were hunting so Charlie had time to swiftly chop its head off with her greatsword.

"Thanks, Cas! Let's get this little bastard back to camp," Charlie replied, picking the dead animal up and slinging it over her shoulders, completely ignoring the blood that started dripping down the back of her tunic.

XXX

" _Alright_! You guys caught dinner!" Dean exclaimed happily when he spotted his friends returning to the campsite.

"Yup. And you guys are cookin' it!" Charlie replied, smirking at the look of indignance on her friend's face.

"Dude, I don't know how to cook a whole boar!" Dean attempted to reason, staring at the dead animal as if it was some great mystery of science he was expected to solve

"Move over then, boy," Bobby spoke up, drawing a dagger out of his boot and moving over to where Charlie had dropped the animal's carcass.

XXX

"Wow, Bobby, this is fuckin' awesome!" Dean exclaimed, tearing another large chunk of meat off the leg of the boar he was eating.

"Thanks, boy," Bobby said, tearing another leg off of the boar and biting into it.

"Yeah, Bobby, s'amazing!" Sam added.

"Thank ya', Sam, now enough with the damn compliments, ya idjits-"

A deafening howl followed by a guttural growl interrupted Bobby's speaking, he turned his head and laid eyes upon a hulking wolf skulk out of the trees, followed closely by a few more.

"Guys! Get in formation, we got wolves to kill!" Dean ordered, grabbing his Morningstar and moving into position with the rest of his party.

Cas readied his glaive and before he managed to swing it, was knocked down onto his stomach by one of the wolves he failed to notice.

"Cas!" Charlie exclaimed, running over and decapitating the creature with her greatsword, reaching out a hand to help the Tiefling up. "You okay?" She added, flashing him a small smile before moving away to keep exterminating the intruding creatures.

Cas raised his glaive again -making sure to keep an eye out for any more wolves this time- and bifurcated a particularly large canine.

"Keep your chin up, kiddo!" Bobby encouraged him, throwing his war pick between the eyes of one of the wolves.

"I am thousands of years older than you, Bobby."

"Shut up and stab!"

XXX

The party paused, all panting from the effort of slaughtering the wolves.

"Did we get 'em all?" Dean inquired, looking around for any traces of the animals.

"I... I think so," Sam replied, still attempting to catch his breath.

"What the fuck did those things want?" Dean queried, relaxing slightly now that he had looked around and seen that all the beasts were dead.

"I got no idea, but somethin' tells me we should leave this damn forest as soon as the sun comes up. Dean, you take the first watch. Sam'll take the second, Cas'll have the third. You'll switch every four hours. Got it?" Bobby said, leaving no argument from any of his boys. The three men nodded, Dean went to sit under the tree they were camped by and the rest of the party got settled in to sleep for at least a few hours.

XXX

" _Sammyyyyyy..._ Come on little bro, I wanna sleep!"

Sam blinked his eyes open and was met with the smirking face of his older brother, gently shaking his shoulder.

"Nnngggg... Okay, hang on a sec, lemme jus'... Lemme jus' get up here..." Sam mumbled, rubbing his eyes with the heels of his palms.

"You got it, Sammy, I'm goin' to bed, see ya' in the morning," Dean replied, patting his brother twice on the shoulder before getting up and moving towards the pile of furs that had become his bed.

Unfortunately, Sam had already fallen back asleep and never took his watch.

XXX

"SAM!"

Sam blinked his eyes open and was met with his brother's angry green eyes, jaw clenched and a furious scowl on his face.

"Sam... Would you care to explain to me... _WHERE THE HELL CHARLIE AND BOBBY ARE, AND WHY CAS IS OUT COLD_?!" The elder Winchester shouted, eyes seeming to burn with the pure rage in his tone.

Sam gulped, glancing around their campsite to confirm his brother's statement, indeed seeing that Charlie and Bobbby were nowhere to be found, and Cas was lying, unmoving, in his blankets.

"I'm waiting..." Dean growled.

"I... I fell asleep! Dean, I honestly don't know what to say... I fucked up, man..." Sam stuttered out, giving his brother his best puppy eyes.

"Damn right you did." Came the still growled reply.

"Is... Is Cas _okay_? I mean like... He's alive right?"

"Far as I know... He's got a steady pulse and he's breathing fine but... I dunno he just won't wake up..." Dean's voice had gradually gotten quieter, almost dropping to a whisper at the last part. His brother was clearly worrying and Sam was honestly right there with him. The younger Winchester got up, now fully awake, and walked over to the unconscious Tiefling, lightly slapping him in the face and frowning when all it did was make his head turn limply to the side.

"What're we gonna do, Sammy?" Dean asked from behind him.

"I have no idea, Dean... I have no idea..."

The glint of something shiny caught his eye, moving over to investigate he crouched down and picked up "a Snickers wrapper?"

 **A/N: I also don't own Snickers (duh) and I'm pretty sure you guys'll be able to guess who's behind the mysterious reduction in party members... What the hell has Gabriel done now?! (And don't worry, guys Cas is gonna be fine, I'm not _that_ mean...) **

**XOXO -KittyKat757**


	7. chapter 7

Castiel let out a small groan as he slowly began to regain consciousness, opening his eyes and becoming confused when all he saw was Dean's back.

"Dean... What... What's going on?" The Tiefling asked quietly, voice still thick from sleep.

"Cas? Oh, thank fuck!" The half-Orc exclaimed, he stopped walking and turned his head to confirm that his friend was indeed awake. "Are you okay, buddy?" He asked.

Castiel nodded, startling a little when Dean hiked him up, the Tiefling just now realising he was piggybacking on his friend.

"Can you walk on your own?" The elder Winchester asked, tightening his hold on Castiel slightly since he didn't want him to fall. When all he received in reply was a garbled mumble, he smiled slightly. "I'll take that as a no..." He added fondly, starting up his stride again since Sam hadn't noticed that Castiel had woken up.

"Hey! Sammy! Cas is-" Dean was cut off when the Tiefling groaned and curled up on Dean's back more than he already had. "Oops, sorry, Cas, guess you must have a bit of a headache, huh?" He apologised, dropping his voice to a whisper so as not to disturb Castiel further.

The latter nodded at his question and groaned again, "Dean, can I go back to sleep, please? I... I'm exhausted," he pleaded softly.

"Sure, Cas, we'll fill you in on what ya' missed when you're feeling more up to it," Dean replied, tightening his grip on the Tiefling again when his breath evened out, and he slipped back into deep sleep.

"So anyway, Sammy," Dean said, trotting up next to his brother while being careful not to jostle Castiel, "Cas woke up for a minute or two there, he was kind of out of it, but at least he's okay, far as I can tell at least."

Sam nodded wordlessly, expression flooding with relief, then smiled, amused at the fact that Castiel had started to drool on the place where his head had become pillowed on Dean's shoulder.

His brother noticed this, and glanced at the sleeping Tiefling, "son of a bitch!"

XXX

Charlie opened her eyes and yawned, stretching her arms above her head and looking around for the camp, becoming alarmed when she found that she and Bobby were in the living room of what looked like a small log cabin.

"What the Frodo Baggins?!" She exclaimed, shaking Bobby's shoulder, rolling her eyes when all he did was grumble angrily and swat at her hand.

"Ah, good, you're awake, I was starting to get bored," a cheerful voice sounded from behind her. She turned around quick as lightning on the heels of her boots and came face to face with Gabriel, letting out a small 'eep' noise when she recognised the now somewhat familiar figure.

"Nice to see you again, Charlie," Gabriel said, smirking and extending a hand for her to shake, when she didn't take it he rolled his eyes. "Relax, I mean you no harm, oh great queen of moons," he added, giving her a small bow, raising his head while still bent over and smirking at her again, whiskey coloured eyes glittering with amusement.

"Why are we here?" Charlie asked.

"Honestly? You guys were thriving a little too well, so I, being the genius that I am, shook things up a little." Gabriel's face screamed triumph at the moment, no doubt remembering whatever he had done in minute detail thanks to angelic memory.

"Where are the others?" Charlie added, deciding that, as long as the archangel was answering questions, she'd keep asking them.

"Back at your camp, I was kinda considering taking Cassie too, but I figured I'd given him enough shit for now already, so I just knocked him out for a day or two, the kid needs to get some sleep anyway."

"Okay... So what exactly is your plan here? Leave clues for the guys to follow to find Bobby and me, then, I don't know... Wait for Dean to swear at you for a solid four sentences, punch him in the face and then leave laughing?" Charlie's fears were beginning to ease up a little bit, she had loved the plot twist in the Supernatural books when it was revealed that The Trickster was an archangel in disguise, and she was beginning to see that Gabriel only harmed those that had committed some form of wrongdoing.

"Basically, yeah," the archangel answered with a shrug. "But for now, you want something to eat? I've got cheesecake if you want some," he tempted, waggling his eyebrows at the redhead.

"Dude, I would _love_ some cheesecake," Charlie replied earnestly, following Gabriel into the cabin's kitchen.

XXX

Dean glanced over at Cas, still sleeping peacefully, and then turned back to the fire that was providing the only light in the small clearing where they were currently camped out. It'd been such an immense relief when Cas had woken up that first time, after being out for roughly a day and a half, that he hadn't thought about the consequences of the Tiefling falling asleep again. What if that was their one chance to get him to wake up properly and that was it? That because they hadn't he would just sleep forever?

"He's gonna be fine; you know that, right?" Sam said, seeming to read his mind.

"It's just... I'm worried, Sammy, that's all. I'm sure I'm just paranoid," Dean replied with a dismissive wave of his hand, though that did not seem to deter his moose of a brother, the perceptive son of a bitch.

"Wait, what are you doing? Sammy?"

Sam walked over to the dozing Tiefling and abruptly kicked him in the side, causing said Tiefling to startle and yelp at the sudden and unforeseen pain.

"Sam, what the fuck, What was that for?!" Dean exclaimed incredulously, staring -feeling guilty somehow even though Sam was the one who'd kicked him- at Cas as he rubbed his now sure to be aching side, looking at the Elf in front of him with undisguised betrayal in his eyes.

"Sam, why did you kick me? Did I somehow do something wrong while I was sleeping?" Cas asked, ' _just like him_ ,' Dean thought, ' _taking the blame even if he had nothing to do with it_.'

"No, just wanted to prove to Dean that you were gonna wake up again, sorry, man," Sam explained, his apology sounding sincere.

"You coulda' done it more gently, you dick! Sorry, Cas, if I had known he was gonna-"

"I-it's fine, Dean... I'm sure I needed to-" Cas let out a long yawn, blinking his eyes rapidly in an attempt to fend off the drowsiness that was trying to retake him. "-Wake up soon anyway," he finished, rubbing his eyes with the heels of his palms.

"No, Cas, go back to sleep, you need the rest. This time I'll make sure nobody _kicks you again_ ," Dean replied, glaring at his brother, who merely shrugged guiltily.

"But-"

"Cas, do not make me knock you out myself."

Cas nodded, accepting the fact that he wasn't winning this one, yawned again, and settled back into the pile of furs Dean had set him down on when they had made camp for the night.

Once Dean made sure that Cas was asleep again, he turned back to Sam, "dude, what the hell was that?!" He whisper-yelled.

Sam shrugged again, "was just convincing you that he was gonna wake up again, and besides, I didn't mean to kick him _that_ hard."

"Judging by his reaction it seemed to be pretty painful," Dean pointed out, still scowling at his stupid brother.

"Look I didn't mean to, okay? And besides, at least now we know he's just really, really tired and not out cold for the rest of his life, right?"

Dean scowled, trust Sam to find the logic in kicking someone in the side while they were sleeping.

His brother seemed to read his mind once again and smiled triumphantly, picking up the stick he had set down before waking Cas and poking at the fire.

XXX

"So wait... You put them in one of those over-complicated Japanese game shows and hit Sam in the nuts with a ball?" Charlie asked, shoving a forkful of cheesecake into her mouth.

" _Yup,_ " Gabriel replied, popping the 'p' and smiling triumphantly.

"Nice," Charlie laughed, setting her plate down on the coffee table and looking over to where Bobby was still sound asleep. "So wait, he's gonna wake up soon, right?"

"He can wake up whenever he wants to, I think he just needs the extra sleep," Gabriel said with a shrug.

"Makes sense, I would need fourteen hours a night if I had to deal with the guys almost every day..."

XXX

"Cas? Cas, buddy, I need you to wake up for me, okay? Can you do that?"

Castiel cracked open one eye and was met with Dean's gently smiling face.

"Hey, bud," he said, ruffling Castiel's hair, "sorry to wake you, but you gotta eat something, I don't want you starving to death on us," he added, standing up from his previous crouching position and helping his friend to sit up. "There ya' go," he praised, ruffling the Tiefling's hair again and going over to the small stash of supplies to collect some food.

"H..." Castiel yawned, "how long have I been sleeping?"

"Doesn't matter, once you're done eating I'll let you go right back to dreamland, deal?" Dean dismissed, handing Castiel a small canteen full of water and some dried meat and berries. "Yeah, I know it ain't much, but Sammy an' I have no idea how to hunt wild animals, and your ass has been knocked out about ninety-six percent a' the time we've been camped out in this forest," he explained. Castiel nodded and gratefully took a sip of water, then began to eat the food Dean had given him.

"Wait a minute... Dean, Where are Bobby and Charlie?" Castiel asked, just noticing that he hadn't seen the redhead or the Winchesters' surrogate father either of the times he had woken up after his mysterious unconsciousness had set in.

"Uh, yeah, about that... We think. We think that. _Gabrielmighta'taken'em_ Dean mumbled out the last part, but Castiel heard it, all the same, he would've sprung up from the furs he was lying on if not for Dean's hand on his chest.

"Easy, Cas. He did something to you too, and you need to take it easy, okay?" It was more of an order than a question, but that didn't stop Castiel from trying to get up again, only to be held down more forcefully by the half-Orc. "I'm serious. I wasn't joking before about knocking you out again myself if you didn't try and get back to sleep voluntarily. Sleep."

Castiel sighed, once again knowing he wasn't going to win this argument -plus he didn't exactly want to try testing Dean's patience at the moment, in his weakened and drained state- and closed his eyes, drifting off to the feeling of Dean running his fingers through his hair.

XXX

 **A/N: you got me... I'm a massive sucker for sleepy!Cas... Stone me, hang me, mock me if you will, but he is just such an adorable little bean, and I couldn't resist makin' 'im all sleepy an' cute to go along with that... Oh well. I'm gonna be writing a Christmas fic probably, with Destiel and Sabriel (because I hardcore-ship them too) which'll just be a giant holiday fluff piece self-indulgence big-ass ball of holiday mush. So yeah, look forward to that I guess... My DnD campaign currently (we stopped the last one btw, and I have a new character who is a gay fire genasi bard named Tristen) is going nowhere atm because it ties into the campaign of the other group in our club (if that makes any fucking sense) and they aren't as far along as we are so right now we're basically just playing guildhall home makeover... Anyway, see you soon, my lovelies!**

 **-You all bloody well know who this is by now.**


	8. chapter 8

"Cas? Cas, buddy? Can you wake up for me?"

"No."

"Cas, C'mon... We gotta get moving again, okay?"

Castiel huffed, snuggling deeper into his blankets and pointedly ignoring his half-Orc friend.

"Ugh, fine, if that's how you want it, then, Cas," Dean grumbled before scooping the Tiefling up while he was still swaddled in furs and placing him gently over his shoulder. Castiel huffed again and relaxed into Dean's hold, confident that he wouldn't drop him or jostle him too much.

"You're really just gonna sleep on my shoulder, huh?" Dean asked amusedly, a fond smile on his face as he carried the Tiefling over to where Sam was finishing up the dismantling of the camp.

"Yes, if you don't mind..." Castiel replied sleepily, already starting to drift off again.

"Fine. Sweet dreams, Cas."

Castiel grunted in acknowledgement before his eyes slid shut and he fell asleep on Dean's shoulder.

XXX

"So, Gabriel? How did you survive? I mean I read the book where Lucifer stabbed you, and admittedly I cried," Charlie asked, setting down the cup of tea she was holding in her hands.

"Oh please... How many times have I faked my death? You really think I wouldn't have an escape plan set up, just in case?"

"Yeah, okay, that was a stupid question... But wait, you never showed up again after that until now, right? Why?" Charlie questioned.

"I didn't want to show up again until the apocalypse was over with, eventually I just kinda forgot to talk to the Winchesters or my little bro until now," Gabriel answered with a shrug.

"Wait so were you drawn to us while we were playing DD or did you just decide to pop in, saw us playing and then thought 'oh, they're playing a fantasy RPG, y'know what'd be fun, Transporting them into it'?" Charlie asked confusedly.

"Pretty much, yeah," Gabriel admitted with a shrug, "that and I thought you guys all kinda needed a break, just because I haven't popped in doesn't mean I haven't been keeping tabs on you, more for Cassie's sake than anything, but still."

Bobby gave a snort and rolled over, grumbling something in his sleep about idjits never letting him get any damn rest.

"Okay, that's it I'm waking him up," Charlie said adamantly, "Bobby! Get your lazy dwarven ass off the couch!"

Gabriel burst into laughter at that, clutching his stomach as he giggled for a solid thirty seconds thanks to the redhead, who smiled triumphantly at the fact that she'd made an archangel laugh.

"The hell'd you- oh, Charlie, it was you... I won't mouth off to ya' 'cause I know it won't do anything, but you oughta show me more respect, girlie." Bobby scolded before his eyes landed on Gabriel. "The hell's he doin' here? Where're the boys?"

"Long story short, he kinda snatched us from the camp and apparently knocked Cas out for a couple of days..."

"Speaking of, I should probably let the spell start to wear off properly now, I've been monitoring him and he's been waking up for short intervals and then passing out again throughout the entirety of the last two days," Gabriel said before snapping his fingers and turning to the angry bearded dwarf on his sofa. "And as for you, Thorin." He smirked at his own joke, "chill the hell out, I'm not hurting anyone while you two are here, honestly, me and Charlie have just been talking for the last few hours."

"Fine, whatever, I don't care... Ya' got any booze in this place, feathers?"

Gabriel smiled, "what's your poison?"

XXX

Dean grunted as he shifted Cas slightly on his shoulder, considering moving him onto his back again since at least then the weight would be balanced properly.

"Dean, stop. I hear something..." Sam said abruptly, throwing out his arm to stop Dean in his steps and listen intently to the sunny forest around them.

"I don't hear anything..." Dean said after a few minutes, rolling his eyes at his brother's paranoia and continuing his trek along the path.

Almost as soon as he said this, the sound of a lute filled the area around them. Figures.

"Oh fuck, what now?..." Dean sighed angrily, grabbing the handle of his Morningstar and shifting Cas to a more secure position across his shoulders.

"I dunno, sounds-"

Suddenly, a man that bared a striking resemblance to Robin Hood, except wearing all magenta and pink, jumped out of the bushes, strumming a loot and grinning like a maniac at the three men.

"Oooookay..." Dean said, raising one eyebrow in confusion at the strange sight in front of him.

"Greetings, half-Orcs, Elves, and Tieflings alike! I am Lucius! Lucius Farghorn!" The man greeted, his voice annoyingly chipper.

It took Dean a couple of seconds to remember how to form words again, remembering to rank this pretty high up on the list of weirdest things he'd ever seen. "Can I help you?" He asked, frankly still quite bewildered by this unexpected encounter.

"No, but you can help my friend here..." Lucius said before he smirked and his demeanour turned from happy to sneaky and cunning. A man in dark, mostly leather clothing leapt out from the bushes beside him and began rushing towards the brothers, using their momentary confusion to his advantage.

"Son of a bitch!" Dean cursed, fully drawing out his Morningstar while Sam readied his battleaxe. Although they expected the newcomer to attack them, they were surprised when he jumped over Dean's shoulder, snatching the sleeping Tiefling from the half-Orc's grasp and grinning at his success.

"Hey! Put him down, you rat bastard!" Dean snarled. The rogue's grin widened and he shook his head, maneuvering away from the Winchesters' attempts to tackle him and trotting back over to his companion.

"Pleasure doing business with you, boys! Tieflings are rare where we come from and this one will bring us a pretty penny! Ciao!" Lucius said cheerily, smiling wolfishly and waving at the Winchesters.

It was luckily, at that moment that Castiel started to stir, groaning and wriggling around a little, finally opening his eyes and staring confusedly at the unfamiliar person who had a hold on him.

"Cas! No time to explain right now, just fuck these guys up!" Dean bellowed. That seemed to get the Tiefling's attention, as he immediately wriggled out of the rogue's grip and knocked him to the ground.

"Dean, Glaive!" He ordered quickly, catching the heavy, double-bladed weapon with ease when Dean threw it to him, using it to speedily kill the two men he was fighting. He dropped his fighting stance now that the danger was out of the way and yawned, clearly having used up what little energy he had.

"Whoa... Cas, that was awesome! Sorry that slippery bastard managed to grab ya' from me, kinda took me by surprise..." Dean said, rubbing the back of his neck in embarrassment towards the end of his sentence.

"It's okay, Dean, why didn't you attempt to wake me when they showed up?" Castiel asked curiously, using the cloth of Lucius' shirt to wipe the blood off of his weapon.

"I wasn't sure if you would... I mean you've been sleeping pretty much non-stop since Charlie and Bobby disappeared, figured whatever Gabriel hit you with hadn't worn off yet," Dean explained truthfully.

"It hasn't fully, but I believe I will be able to stay awake for a longer period this time, but I have no idea how long I will sleep for once I lose consciousness again," Castiel replied, securing the glaive to his back and rejoining his companions.

"Sounds like a plan," Dean sighed, "c'mon, let's get going again, don't wanna run into any more weirdos..."

XXX

 **A/N: Hello! Just a quick little author's note because I should be heading to bed about now, sorry if there are any spelling or grammatical errors in this chapter, my Grammarly is being an asshole and I can't get free premium (WAH!) so I have to stick with the shitty version.**


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